


First Time's the Charm

by KaitlynSpeight



Series: Tumblr Prompts [25]
Category: Supernatural
Genre: Anal Sex, Dean is a Little Shit, Established Relationship, First Time, M/M, Rimming, Schmoop
Language: English
Status: Completed
Published: 2017-03-01
Updated: 2017-03-01
Packaged: 2018-09-27 17:54:10
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 876
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10037207
Author URL: https://archiveofourown.org/users/KaitlynSpeight/pseuds/KaitlynSpeight
Summary: DeanxBenny first time?





	

**Author's Note:**

> Yes hi hello porn is not my thing so I apologize ahead of time but it was DENNY I can't not fill Denny it's the truest of all the OTP's and I will absolutely go down with this ship

“Jus- Don’t do nothin’ sappy alright, man? I’m not into all that… Whatever… shit.” Dean grumbled when Benny finally lowered him down onto the bed.

 

And it was about damn time too - they’d been together for almost a year, longer if you counted purgatory (Sam did), and Benny’d moved into the bunker months ago… Still, Dean’d been nervous as hell, not that he’d ever admit it, but Benny’d never push him, and so Dean never had to make himself do anything he wasn’t ready for.

 

“Yeah yeah, shut up will ya?” Benny grinned, gently guiding him into a kiss and slowly pressing his hands under his shirt.

 

“Bear- really just… Give it to me alright? I don’ need none o’ this…” Dean pouted up at him, not that he’d ever call it a pout, and he’d probably shoot anyone that did.

 

Benny snorted, shaking his head. “Fine. Strip, on your stomach, jus’ let me know if you wanna stop.” With that he sat back, giving Dean room to do as he was told.

 

It took him a minute, but Dean eventually listened, hesitantly glancing at his boyfriend before hiding his face against the blankets. “That’s better… jus’… Get to it.”

 

Benny rolled his eyes, gently kissing along the back of his neck and stroking his hands over his hips. “Knock it off will ya? It’s not like you’re a girl, I can’t just shove it in unless you wanna be bleeding for the next week.”

 

Dean grumbled, but stopped protesting as Benny’s hands slowly skated up his sides.

 

Benny smiled softly, lightly kissing a trail down his back, “that’s more like it, spread ‘em, sug… lemme see you.” He gently tapped Dean’s thigh, licking over the soft dip in his back.

 

Dean hesitated, slowly spreading his legs further apart and glancing over his shoulder. “W-what are you doing back there..?”

 

“You jus’ relax, let me take care o’ ya, cher.”

 

Dean nodded slowly, dragging a pillow under him and hiding his face.

 

Benny snorted, spreading him open and licking a stripe over his hole, keeping his hips pressed firmly into the mattress when he tried to buck away.

 

“Dude what the hell are you-”

 

“Just hush, will ya,” Benny growled, burying his face and going to town until the only sounds coming from Dean were soft mewls and whimpers.

 

He smirked, grabbing the lube he’d stashed earlier and slowly working a finger into him, then another, pausing every time Dean tensed under him.

 

By the time he had four fingers in him Dean was a sobbing mess, shuddering and squirming under him as he kissed back up his spine.

 

“O-oh God… Bear please… Need you- please…”

 

Benny chuckled, slowly working his fingers free and peppering his shoulders with kisses. “Of course cher, just relax for me…”

 

Dean sobbed, reaching back and grabbing onto Benny’s hip, trying to pull him closer as he lined up and slowly pressed in.

 

“So good sug, I’ve got ya,” Benny murmured, gently stroking his flank until Dean settled under him, heaving a ragged breath before turning so he could see him.

 

“‘M good… Please jus’…”

 

Benny smiled, gently kissing his cheek before pulling out and rocking into him. “God you’re so tight doll…”

 

Dean whined, clenching around him and pressing back to meet his thrusts. “So good bear… Love you- o-oh God just like that…”

 

“Love you too cher… Make such a pretty picture like this,” he chuckled softly, hooking an arm around his chest and pulling him back into kiss, slowly stroking his cock.

 

“Holy shit- Benny… Don’t stop…”

 

“Wouldn’t dream of it,” Benny murmured against him, snapping his hips forward.

 

“Again! Oh fuck, just like that- please- need to come.”

 

Benny groaned, pressing his forehead to Dean’s shoulder as he plowed into him, striping his cock. “Let me see you cher, be a good boy and come on my cock.”

 

Dean cried out, arching back into him as he came hard before slumping boneless onto the bed.

 

Benny smiled softly, stilling his hips. “Good boy s-”

 

“Don’t you dare stop… Wanna feel you, please Ben- wanna be yours…” Dean whined, trying to ignore how his voice cracked.

 

Benny hesitated for a moment before slowly regaining a rhythm, kissing everywhere he could reach. “You are mine, all mine… Love you so much.”

 

Dean whimpered, leaning into the touch and squeezing his eyes shut. “L-love you too… Please…”

 

Benny groaned, dragging him into a kiss as he came. It took another minute to gain enough brain power to roll off him, immediately pulling him tight against his chest and kissing his forehead. “Was ‘t okay?”

 

Dean glanced up at him, raising an eyebrow. “Don’t think I’ve ever come so hard in my life… We’re definitely doing that again.”

 

“Course we are, cher,” Benny snorted, softly kissing his eyelids and wiping the tear stains from his cheeks. “Get some rest, if you’re up for it we can go for round two in the morning.”

 

Dean smiled shyly, snuggling closer and letting himself go boneless in Benny’s embrace, “it’s a date… I’m always up for great sex… I love you.”

 

“Thought you didn’t wanna be all sappy.” Benny teased, laughing when Dean slapped his chest. “Alright alright, I love you too sug, goodnight.”


End file.
